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Curable polycyclic compounds and process for the production thereof

a polycyclic compound and polycyclic compound technology, applied in the field of cureable polycyclic compounds, can solve the problems of limited application and limited knowledge of cureable compounds, and achieve the effects of improving heat resistance and light resistance, reducing shrinkage, and improving optical properties

Inactive Publication Date: 2006-11-09
TOKUYAMA CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0017] These compounds, when cured, give a cured material high in optical properties and light resistance. It was further found that these compounds give a small shrinkage when cured and, therefore, can be suitably used as an adhesive or an encapsulant for semiconductor laser, both requiring optical properties, high heat resistance, etc.
[0026] The curable polycyclic compounds of the present invention are characterized by giving a cured material superior in optical properties, heat resistance and light resistance and being small shrinkage when cured. Therefore, the compounds can be suitably used as a raw material for various plastic substrates, a raw material for coating, a raw material for adhesive, a raw material for encapsulant, etc.
[0027] The cured material of the curable composition of the present invention is superior in light resistance, heat resistance, etc. and has high adhesivity to light-emitting diode. Therefore, the curable composition of the present invention is suitable as an encapsulant for short-wavelength LED (e.g. near-ultraviolet LED or white LED), etc.

Problems solved by technology

In other words, the method of curing a curable compound containing a polycyclic hydrocarbon skeleton, to obtain a resin, is promising as a useful means for obtaining a resin superior in optical properties and heat resistance; however, such curable compounds currently known are limited and accordingly their applications are limited as well at the present stage.

Method used

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  • Curable polycyclic compounds and process for the production thereof
  • Curable polycyclic compounds and process for the production thereof
  • Curable polycyclic compounds and process for the production thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 1,3-bis[(3-ethyloxetan-3-yl)methoxy]adamantane

[0128] 300 ml of dehydrated tetrahydrofuran containing 16.8 g (0.1 mol) of 1,3-adamantanediol and 5.3 g (0.22 mol) of sodium hydride was stirred in a nitrogen atmosphere at the reflux temperature for 2 hours. Thereto was dropwise added 56.4 g (0.22 mol) of 3-ethyl-3-p-toluenesulfonyloxymethyloxetane. 36.5 g (0.22 mol) of potassium iodide was added. The resulting mixture was stirred at the reflux temperature for 12 hours. To the reaction mixture was added 200 ml of chloroform. The mixture was washed with water, and the chloroform layer was dried with magnesium sulfate.

[0129] The dried chloroform layer was subjected to distillation under reduced pressure for solvent removal, whereby was obtained a white solid and oily matter. This was purified by silica gel column chromatography to obtain 2.39 g (yield: 7.1%) of a white solid and oily matter. This compound was subjected to MASS spectrometry, 1H-NMR spectrometry and elemental...

example 2

Synthesis of 2,5-bis[(3-ethyloxetan-3-yl)methoxy]norbornane

[0136] 300 ml of dehydrated tetrahydrofuran containing 12.8 g (0.1 mol) of 2,5-norbornanediol and 5.3 g (0.22 mol) of sodium hydride was stirred in a nitrogen atmosphere at the reflux temperature for 2 hours. Thereto was dropwise added 56.4 g (0.22 mol) of 3-ethyl-3-p-toluenesulfonyloxymethyloxetane. 36.5 g (0.22 mol) of potassium iodide was added. The resulting mixture was stirred at the reflux temperature for 12 hours. To the reaction mixture was added 200 ml of chloroform. The chloroform layer was washed with water and then dried with magnesium sulfate. The dried chloroform layer was subjected to distillation under reduced pressure for solvent removal, whereby was obtained a white solid and oily matter. This was purified by silica gel column chromatography to obtain 1.39 g (yield: 4.71%) of a white solid and oily matter. This compound was subjected to MASS spectrometry, 1H-NMR spectrometry and elemental analysis. From th...

example 3

Synthesis of 5,7-dimethyl-1,3-bis[(3-ethyloxetan-3-yl)methoxy]adamantane

[0143] An operation was conducted in the same manner as in Example 1 except that 16.8 g (0.10 mol) of 1,3-adamantanediol was replaced by 19.6 g (0.10 mol) of 5,7-dimethyl-1,3-adamantanediol, whereby was obtained 2.70 g (yield: 7.4%) of a white compound and oily matter. This compound was subjected to MASS spectrometry, 1H-NMR spectrometry and elemental analysis. From the results of the analyses, the compound was confirmed to be intended 5,7-dimethyl-1,3-bis[(3-ethyloxetan-3-yl)methoxy]adamantane. The results of analyses are shown below.

[0144] MASS (EI): molecular weight 364 (M+)

[0145]1H-NMR: δ 1.1-2.0 (m, 24H), 2.6-4.1 (m, 12H)

[0146] Elemental analysis: as C22H36O4

[0147] Calculated: C 72.49, H 9.95

[0148] Measured: C 72.87, H 9.88

[0149] The compound was measured for inorganic chlorine content by the method for determination of saponifiable chlorine, described in ISO 4583 and the method described in ISO 4573...

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Abstract

The present invention discloses a curable polycyclic compound represented by the following formula (1): {wherein A is a di- to hexa-valent group derived from a polycyclic hydrocarbon compound; R1 is an alkyl group of 1 to 4 carbon atoms, a perfluoroalkyl group of 1 to 4 carbon atoms, or a fluorine atom; n is an integer of 0 to 2; m is an integer of 2 to 4; and Y is a group represented by the following formula (2) or (3): (wherein R2, R3, R5 and R6 are each independently a hydrogen atom, a fluorine atom or an alkyl group of 1 to 4 carbon atoms; R4 is a methyl group or an ethyl group; and p and q are each independently an integer of 0 to 4)}.

Description

TECHNICAL FIELD [0001] The present invention relates to novel curable polycyclic compounds useful as a raw material for encapsulant, adhesive, etc.; a process for production thereof; a curable composition prepared using the compound; an encapsulant for light-emitting diode, comprising the curable composition; and a light-emitting diode encapsulated with the encapsulant. The curable polycyclic compounds have oxetanyl group or epoxy group as a functional group capable of giving rise to a curing reaction. BACKGROUND ART [0002] Polycyclic hydrocarbon compounds show non-aromaticity, have a stiff molecule, have a unique structure and accordingly are drawing attention in various fields. There are known, for example, diallyl adamantanedicarboxylate (JP 1985-100537 A) and adamantanedi(meth)acrylate derivatives (JP 1988-307844 A), each as a monomer for plastic lens superior in optical properties and heat resistance. [0003] There are also known particular adamantane compounds having (meth)acry...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C08G65/04C07D407/02C07D305/02C07D303/27C07D303/28C08G59/30C08G59/32H01L23/29H01L33/24
CPCC07D303/28C08G59/30C08G59/3254H01L2924/0002H01L33/24H01L23/293H01L2924/00C07D303/27C07D305/06
Inventor TAKENAKA, JUNJIYAMAMOTO, HIROMASATANAKA, KENJI
Owner TOKUYAMA CORP
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